Ruthenium(IV)-catalyzed markovnikov addition of carboxylic acids to terminal alkynes in aqueous medium

  • Cadierno V
  • Francos J
  • Gimeno J
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Abstract

The dimeric bis(allyl)ruthenium(IV) complex [{RuCl(?-Cl)(?3:?3-C10H16)}2] (C10H16 = 2,7-dimethylocta-2,6-diene-1,8-diyl) (5) and several mononuclear species trans-[RuCl2(?3:?3-C10H16)(L)] (L = two-electron-donor ligand) (6) derived from 5 have been checked as catalysts for the addition of carboxylic acids onto terminal alkynes using water as a green reaction medium. The best results in terms of activity and regioselectivity were obtained with the mononuclear derivative trans-[RuCl2(?3:?3-C10H16)(PPh3)] (6a), which was able to promote the selective Markovnikov addition of both aromatic and aliphatic carboxylic acids to a large variety of terminal alkynes, enynes, and diynes as well as propargylic alcohols. In this way, a wide number of enol esters and ?-oxo esters could be synthesized in moderate to good yields under mild conditions (60 °C) in an aqueous medium.

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